Carbocation

From Academic Kids

A carbocation is an ion with a positively-charged carbon atom. A carbocation was previously often called a carbonium ion but questions arose on the exact meaning [1] (http://www.iupac.org/goldbook/C00839.pdf). The charged carbon atom in a carbocation has only six electrons in its outer valence shell instead of the eight valence electrons that ensures maximum stability (octet rule). Therefore the carbon cation is unstable and very reactive, seeking to fill its octet of valence electrons as well as regain its neutral charge.

The history of the science of carbocations goes back to 1902 when chemists Norris and Kehrman independently discovered that colorless triphenylmethyl alcohol gave deep yellow solutions in concentrated sulfuric acid. Triphenylmethyl chloride similarly formed orange complexes with aluminum and tin chlorides. Adolf von Baeyer recognized in 1902 the salt like character of the compounds formed.


Ph3C-OH + H2SO4 → Ph3C+HSO4- + H20 (Ph stands for a phenyl substituent)


He dubbed the relationship between color and salt formation halochromy of which malachite green is a prime example.

A carbocation in a chemical reaction is a reactive intermediate. This idea was first developed by Hans Meerwein in his study of the Wagner-Meerwein rearrangement. Carbocations were also found to be involved in the SN1 reaction and E1 reaction and in rearrangement reactions such as the Whitmore 1,2 shift. The chemical establishment was reluctant to accecpt the notion of a carbocation and for a long time the Journal of the American Chemical Society refused articles that mentioned it. In 1962 Olah directly observed the tert-butyl carbocation by Nuclear magnetic resonance as a stable species by dissolving tert-butyl fluoride in a superacid.

In organic chemistry,a carbocation is often the target of nucleophilic attack by nucleophiles like OH- ions or halogen ions.

Carbocations are classified as primary, secondary, or tertiary depending on the number of carbon atoms bonded to the ionized carbon. Primary carbocations have one or zero carbons attached to the ionized carbon, secondary carbocations have two carbons attached to the ionized carbon, and tertiary carbocations have three carbons attached to the ionized carbon.

Primary carbocations are highly unstable and reactions such as the SN1 reaction and the E1 elimination reaction normally do not occur if a primary carbocation would be formed. An exception to this occurs when there is a carbon-carbon double bond next to the ionized carbon. Such cations as allyl cation CH2=CH-CH2+ and benzyl cation C6H5-CH2+ are more stable than most other carbocations. Molecules which can form allyl or benzyl carbocations are especially reactive. Secondary carbocations are formed more readily than primary carbocations, and tertiary carbocations are formed still more readily. Excluding some exceptions like the allyl and benzyl carbocations just mentioned, a primary carbocation is less stable than a secondary carbocation, which in turn is less stable than a tertiary carbocation, although they are all very unstable.

Missing image
Alkyl_carbocations.png
Order of stability of examples of
primary ( I ), secondary ( II ), and tertiary ( III ) alkyl carbocations

A carbocation can undergo a rearrangement from a less stable form to a more stable form in a chemical reaction.

references

http://nobelprize.org/chemistry/laureates/1994/olah-lecture.htmlpl:Karbokation

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